Dress for Success
by widerthandistance5647
Summary: Regina Mills tries to seduce Emma Swan with various outfits with varying degrees of success.
1. Chapter 1

As the Evil Queen, Regina Mills was used to getting what she wanted. As the Mayor of Storybrooke, Regina Mills was still used to getting what she desired, mostly. As Regina Mills, she was used to the things she wanted being torn from her in the worst ways imaginable. That is why, after the trouble with Peter Pan, her half-sister Zelena, and the Ice Queen Elsa was over and Storybrooke had time to breathe, when she realized that she _wanted _something, she approached it with pessimistic resignation. After all, her _destined _happiness with Robin Hood came to an end. How could she expect this to work out?

However, no matter how hard life got, Regina never gave up. That is why she possessed the most resilient heart. So fearing the worst, Regina prepared to go after what she wanted. Because she knew, no matter how slim she thought the reality of achieving her goal was, that the slight possibility she _did _get what she wanted would be more than worth the effort. Since, what she wanted was more a _who _than a what.

* * *

Seduction was an art she became well-versed in as the Evil Queen. And while parading around in the attire she did in the Enchanted Forest, which did wonders for her cleavage, would be unbecoming of a mayor, she realized that this world had more than enough options to suit her means.

Of course, she really did hate leaving the haven of her town. She'd only done it on a handful of occasions since enacting the curse, and aside from the one time, when she was privileged enough to adopt Henry, every time carried with it a bad memory, including the time she almost gave Henry back. Yet there were no options in Storybrooke that would cater to her specific needs. Desperate times call for desperate measures, and while she would not exactly call her quest quite desperate yet, she was prepared to be ready for when it became as such.

So she had arranged for Henry to stay the day with Emma Swan, his other mother, while she went out to Boston to go shopping. Quite meeting her expectations, she met with resistance from the blonde.

"Don't you have enough clothes?" the sheriff regarded her with a raised eyebrow as she gesticulated to Regina's current ensemble, a simple black pencil skirt, a pair of Jimmy Choos, and an off-white silk blouse.

Regina fixed Emma with a practiced, mayoral smile as she answered, "A woman can never have enough clothes, Miss Swan. Something I'm sure _you _wouldn't know, as you seem to have quite the attachment to that one red leather 'jacket' and those jeans of yours."

Instead of getting offended, or worse, bringing up her past as a foster kid who didn't exactly get her pick of wardrobe, Emma just shrugged, "They're comfortable. Something, _I'm sure, _Mayor Mills, you know nothing about."

Her patience was wearing thin and she once again doubted all of the reasons she had mentally worked through to convince herself that her goal was worth suffering through _this. _She huffed, "Are you going to watch Henry today like you agreed or not?"

At this, Emma lit up. "I've got a better idea. Why don't Henry and I go with you?"

Regina's first instinct was to immediately reject the blonde's proposal. She had planned to do this alone, to get what she needed and return home as swiftly as possible. But then an idea occurred to her. She wouldn't give in to the blonde straightaway, of course. She had learned through years of parenting Henry, who was much like his other mother, that giving in immediately would only prove to be a mistake later.

"Why would you want to go to Boston with me to pick out clothes?"

Emma rolled her eyes, "It's not the clothes, really, Regina. But I think it'd be good for me and the kid to get out of town for a while. You know, he and I do miss the way it was in New York."

At this comment, Regina faltered. And Emma picked up immediately on her warring emotions.

"Hey," she soothed, "I didn't mean it like that. Just that, you know, New York was simple and _happy. _For the most part. I do think Henry and I felt like something was missing." At this, Regina received a small smile from the blonde. "But if we _all _go to Boston, the kid, me, _and you, _nothing will be missing. Hmm? It'd be like a family day."

It was ridiculous, Regina knew, to feel the way she did when Emma had used the word 'family' and included her, but she couldn't quite help herself. And she was very near tears, of happiness, but Emma misinterpreted.

The blonde moved to embrace Regina in a sort of half hug as she continued to try to placate her emotions, "Regina, I'm sorry. I don't know exactly what I said, but I didn't want you to cry. I can stay here and watch Henry. You can go have fun on your shopping trip. Just, uh, watch out for yourself."

"I'm more than capable of handling myself, Miss Swan" Regina said, but her attempt at sounding imperious was abysmal, considering she was still sniffling in an attempt to hold back her tears.

"I know. God, _I know," _Emma laughed. "But you won't have magic out there, Regina. And a pretty woman like you in a city like that? I'd feel better if I could keep an eye on you, is all. And I _still _think Henry would like a family day out of town."

Regina wasn't sure if it was Emma calling her pretty, of all things, or her insistence that Henry would enjoy an outing that included her company, or the fact she had already made up her mind to let the blonde and their son accompany her on her trip out of town, but Regina found herself readily agreeing.

"I suppose that your company wouldn't be completely unbearable. And of course, Henry is welcome to spend time with me whenever he likes. _And _considering you used to live in Boston, you would know the area better than I."

Emma snorted, "You don't have to sound so _regal_, Regina. And, really? Could you sound any _more _offended that I _might _know something better than you?"_  
_

"Do you want to come or not?"

Regina had already started walking out of the police station. She had not planned on a 'family' trip and she would have to reorganize her car, because there was no way in hell she was getting in that yellow deathtrap Emma insisted on calling an operating vehicle. What she missed, in her hurry to prepare for the upcoming excursion, was Emma Swan blatantly staring at her ass as she exited the station and muttering under her breath, "More than you know, Regina. More than you know."

* * *

The drive to Boston was quite uneventful. Henry had just started entering the moody teenager stage, and even though he was clearly excited about the prospect of getting away from Storybrooke for the day and getting to spend time with both of his mothers, it was clear that part of him was clearly embarrassed by this eagerness to hang out with his _parents. _

Emma, for her part, had chattered incessantly. It was clear that she was trying to make the trip fun for Regina and Henry, for which the former queen was grateful. Emma had come up with various 'road games' which Regina was proud to say she won, most of the time. The blonde had also regaled the two Mills about the various fun things in Boston that they could see and do, as well as providing entertaining anecdotes about her life there.

"We are," Regina reminded her, "going out to Boston to obtain new clothes. Do remember that we won't have nearly enough time to do all that you propose."

That didn't stop Emma's clear excitement, however. She just answered Regina with a smile and said, "We'll just have to come back sometime then."

Henry had murmured his agreement. The excitement radiating off the blonde having been infectious. Regina stayed silent and smiled at the two, her _family. _

* * *

At the mall Emma had sworn up and down was _the best_, Regina decided it was high time to put her plan into action. While she did enjoy spending time with Henry and Emma, she had a goal to achieve and she would not be put off. Of course, the art of subtlety was a talent hers and she knew not to expose too much right off the bat. So she invited Emma and Henry to the first few stores she had perused, trying out several pairs of shoes and outfits in front of the pair. Henry had squirmed and fidgeted, but been complimentary, nevertheless. Regina was positive Emma would have been much the same, had the blonde not been completely captivated by Regina modeling the various outfits like she was on a runway.

This was good news, Regina decided. It meant her outfit choices would be suitable to seduce and she presently dismissed Emma and Henry.

"You guys can go browsing the mall yourselves," she had said, outside of a Victoria's Secret. "I need to go in here to pick up a few things, and it is no place for Henry."

Until then, Emma had not been aware which store they had stopped outside of. At Regina's remark, she looked and Regina was certain her jaw nearly hit the floor.

"Victoria's Secret?" Emma had choked out. "What do you need here?"

Regina was certain she heard a tinge of jealously lacing Emma's voice, but if so, she could not place what Emma was jealous _of._

_"_If you need to pick up certain _items _yourself," Regina began, "you most certainly may, _after _I do. I'd like you to take Henry away from this store, however. He is too old to accompany the both of us in there." At this, Regina gestured to the few women who were brave enough to bring their toddler sons into the lingerie store. "And he is too young to have his mind filled with these _images."__  
_

Henry had started to protest, his attention being taken with a particularly attractive ad with a model clad in a very skimpy black lace ensemble clearly meant to tie-in to the upcoming Halloween holiday, but Emma had covered his eyes and turned him around.

"Yeah," Emma agreed. "Uh, take your time. I don't need anything. I think I'll take Henry to GameStop or something. Meet you at the food court?"

"Certainly, Miss Swan," Regina said. "That sounds agreeable."

Emma quickly let go of Henry for a second and went up to Regina. "Hey, let me get these for you."

The blonde gently took the bags containing the purchases of the afternoon away from Regina without protest from the brunette, which surprised all three of them.

"Thank you," Regina said.

"No problem," Emma smiled, her arms now full. "Come on, kid. Let's go see if they've got that new game you've been bugging me about."

* * *

After Henry and Emma had left, Regina had made short work of Victoria's Secret. She really only needed a couple things, after all. She picked a very nice blue-green panty and bra set, as well as a matching one in red. She also picked out the perfect red negligee. She was certain the object of her affections would absolutely _drool _over it when the time came. Much to her chagrin, she had to avoid all of the black offerings, since the ensemble in the ad Henry was staring at was apparently the current style and she could just not bring herself to purchase it knowing her son had found it appealing in the least.

Once finished at Victoria's Secret, she had went back to the few stores she had visited with Emma and Henry in tow. The pair had been quite troublesome to shop with. Henry had looked entirely uncomfortable and Emma had a weird habit of touching everything. It was like shopping with two children.

Alone now, Regina had time to really decide what she wanted. A few of Emma's earlier suggestions had been ignored, mostly because they had been utterly ridiculous. But a few of them were quite nice, actually, and Regina had not missed the way Emma had held up the outfit in front of Regina and then slowly checked out her body as she determined that the articles of clothing would look good on the brunette.

Plucking a few of these suggestions up, as well as a few of her own, she went back into the dressing room. Regina made quick work of trying on the clothes and deciding which ones to keep. It was a lot more efficient, and incredibly less fun, to do this without Henry and Emma sitting outside the dressing room, waiting for her.

Once she was satisfied, she quickly texted Emma that she was on her way to the food court and headed out of the store, loaded up with all of her new purchases.

Her phone vibrated almost instantly, _G8 w8i chinese line kid said wz ur fav_

Regina rolled her eyes at the blonde's atrocious spelling and grammar, but she smiled anyway as she made her way back to her family.


	2. Chapter 2

After the shopping excursion to Boston, she had been quite relentless in her pursuit of her goal. She had worn a few of the different outfits she'd purchased, mixed with some of her older ones that she hadn't worn recently. She had been careful to leave the top three buttons of her tops undone, instead of her usual two. She had even hemmed some of her skirts so that they were shorter, bordering on improper. And while people certainly noticed, the one person she had wanted to win over didn't seem at all moved by the new outfits beyond usual.

Regina was frustrated. Usually, it wouldn't take this long to bed someone she wanted. Usually, all she had to do was command someone to get on their knees for her and they would, without hesitation. She was quite beautiful, something her mother had emphasized as she was growing up, and Regina knew how to use that to her advantage. She was also very alluring and even as the Evil Queen, there were countless numbers of people willing and ready to please her.

But she admitted to herself, she did not just want to bed this person she was after. No, she wanted to build a life with this person, and that required a lot more than brief glimpses of toned thighs and full cleavage, no matter how delectable they were. Plus, if she were being honest with herself, none of the people who had ever shared her bed had been able to bring her the pleasure she so sought. She had not been able to experience an orgasm that was not caused by her own hand, although she became quite adept at faking it when the occasion merited itself.

Regina was certain, however, that if she was able to obtain whom she desired, she would not be faking anything. Unfortunately, that did not seem to be in the cards for the present, so she was currently taking care of herself. It was early morning and Henry was with Emma, so Regina felt license enough to take her pleasure into her own hands, an indulgence she rarely let herself have.

As with the few other times she had pleasured herself since realizing that she was in love with someone again, she pictured that person in her mind. And as with those previous times, it did not take her long to reach climax.

She sighed, wishing that her fantasy had been reality. And just like every other time, she got out of bed with renewed determination. She _would _get what she wanted.

She looked in her closet to pick out the perfect outfit, deciding on one of the ones Emma had picked out in Boston. She didn't even bother washing her hands before getting dressed, an action that went against all of her principles of cleanliness, but she hoped that maybe the scent would linger enough to at least attract the object of her affections, if the outfit didn't do the trick.

_Desperate times do require desperate measures after all, _Regina thought to herself.

* * *

Lunch had become a regular occurrence for the mayor and the sheriff. Usually, she and Emma swapped locations, so every other day she was eating in Emma's office or Emma was eating in hers. Currently, Regina was perched quite strategically on the edge of Emma's desk, picking at a salad.

"You know," Emma said, offering Regina her fries, "you don't have to keep ordering the salad if you don't like it."

Regina expertly uncrossed and recrossed her legs, watching as Emma's eyes briefly shifted from her own down to where her skirt rode up briefly, revealing more of her toned thighs. She snatched a fry and slowly brought it up to her lips, once again capturing Emma's attention as the blonde seemed riveted by the fry in her hand.

"I like the salad just fine, Miss Swan," she said, finally placing the fry in her mouth. What she had forgotten, however, is that she had masturbated that morning and the taste of herself was still very much on her fingers. She moaned, slightly, as she tasted herself mingled with the taste of the French fry, almost completely forgetting Emma was still staring at her.

Emma managed to blush and smirk at the same time, as she said, "Seems like you like my fries a whole lot more."

"Yes, well," Regina said, recovering herself, "I refuse to eat unhealthily with as much frequency as you do."

"Please," Emma scoffed. "With a body like yours, I'm sure you could eat whatever the hell you want and not worry about a thing. _And, _I don't know if you've noticed but I take pretty good care of myself."

With this remark, Emma lifted up her shirt to show off her abs to Regina, which caused Regina to promptly start choking on her salad.

"Shit," Emma exclaimed, scrambling up to get behind Regina in order to perform the Heimlich Maneuver. Once the threat of death had passed, Emma sighed in relief. "I'm sorry, Regina. I know people who would die for my abs, but I didn't want to kill you, honest."

Regina would have laughed at that, but she was still recovering herself from the sight of Emma's abdominal muscles, almost dying, and the feeling of Emma still lingering behind her, her hands on her waist.

"I, uh," Regina managed, "think we ought to call this lunch a little short. I'll see you later, Miss Swan."

Emma reluctantly let go of Regina and moved back to her seat, "Um, okay."

Regina couldn't help but feel that Emma sounded a little disappointed. And, fortunately, this time when she left the police station, she did hear Emma say, "That outfit looks really good on you."

* * *

It was Halloween. And she'd been trying to drum up more than passing attraction for _weeks. _This was it. Tonight she was going to get what she wanted or she was going to give up.

Decked out in the best of her Evil Queen attire, thankful she had saved some of it, Regina rang the doorbell of Emma's new place. It was currently the blonde's week with Henry, so Regina had to go to the blonde's to pick up both their son and his other mother or they'd surely be late to Snow White's Halloween party. And while Regina would have been perfectly fine with missing one of the Charming's endless parties, Henry and Emma were quite insistent that she attend. So Regina had donned one of her most _appealing _outfits, deciding that Halloween was the perfect excuse to dress up like the Evil Queen she used to be and hopefully urge her crush (a term she loathed) to make a move.

Henry answered the door and instead of a pleasant hello, he greeted Regina with a roll of his eyes.

"What?" Regina asked, really hating this new attitude Henry seemed to be developing.

"Give it a break, Mom," he said.

"Give _what _a break?"

"Please," he scoffed. "As if it isn't _painfully _obvious what you're doing."

"And just what am I doing?"

Henry quickly looked behind him, making sure there was no sign of his blonde mother, before he whispered, "I know you're trying to seduce Ma."

Regina was shocked, momentarily, at how quickly her son had looked through her when no one else in town seemed any the wiser. But then she remembered that this was the same boy who had seen through her curse and she sighed.

"Do you have a problem with the idea of me and Miss Swan together?"

Henry once again rolled his eyes. "No. And for God's sake, her name is _Emma. _If you want to be with her, you should probably call her by her _name. _And I think you two would be perfect for each other."

"Really?" Regina was noticeably surprised.

"Yeah," Henry smiled, and Regina was pleased to note how much he looked like Emma in that instant. "I think you guys would make each other happy. But _this," _and he gestured to her outfit, "has _got _to stop. You're making Ma crazy."

Regina was intrigued, "I am?"

"_Yes," _Henry insisted. "Every time she's seen you, she just stares. Or worse, she just talks about how hot she thinks you are, and that's _gross. _Remember last week when she came to pick me up and you answered the door in that _dress _and she spent like _forever _staring at you and wishing you'd invite her in? Then we had to have the _most awkward _dinner in the history of _ever_ because all she did was stare at you and compliment you? 'Oh, Regina, your lasagna is amazing. Oh, Regina, that dress looks really _great _on you. Were you planning on going anywhere?'"

Henry crossed his arms. He was not amused. "I wanted to throw up. She was worse than Gramps and Grams on their _worst _days."

"Well," Regina reasoned, "if you're so sure she likes me, why hasn't she made a move?"

Henry laughed, "She doesn't _like _you, Mom. She _loves _you. Like really, really loves you. And she hasn't 'made a move' because she's scared."

"Of me?" Regina was incredulous. Emma Swan had never appeared to be frightened of her before.

"No," Henry replied. "Of herself. She doesn't want to mess anything up."

Regina sniffed, "If anyone is going to mess anything up, it will be me."

Henry's face suddenly turned very serious. "Don't talk like that. _Neither _of you will mess it up. You're perfect for each other. And I've been telling Ma that for forever. Since _before _the curse broke."

"Really?"

Henry shrugged, "Well, yeah. I mean. She's the Savior, you know? White Knight? And you _were _the Evil Queen. I figured out of everyone, you needed the most saving."

Regina was incredibly touched by these words. "Thank you," she whispered.

"Don't mention it," Henry brushed her off. "Now, Ma's been upstairs trying on every single thing she owns to try to impress you tonight and clearly _you've _done all this. Which, thank you for scarring me for life. I think I might be gay now."

"What?" Regina asked, completely uncomfortable thinking of her son as a sexual being in any sense.

"Well," Henry said, clearly debating on whether or not to say anything, "you're pretty sexy, Mom, and this outfit is doing weird things to me. I _am _hitting puberty, and you might have just ruined women for me forever."

Both Mills were in a very awkward silence when Emma Swan bounded down the stairs and toward the front door.

"Hey, kid, when you answer the door, you're supposed to let the person _in."_

But then Emma's jaw dropped and she just stared. She was completely unapologetic as she muttered, "_Damn, _Regina, are you trying to kill me?"

"Not this time, dear," Regina smirked, shaken out of her Henry-induced awkward daze. "You see something you like?"

Hearing confirmation from Henry that Emma actually did return her feelings, Regina was feeling much, much more confident.

"Definitely," Emma nodded vigorously. "You look even better that when I first saw you as the Evil Queen."

"This is gross," Henry interrupted. "Let's go."

Regina just laughed and shook her head. She didn't even get a chance to tell Emma she very much liked her costume as well. The leather pants were quite appealing.

* * *

Unfortunately, Emma did not make a move Halloween night and Regina was seriously about an inch away from going insane. Emma clearly liked her, but obviously subtle was not her style at all, since none of Regina's hints had spurned the other woman into action.

So with Henry in tow, encouraging her to just outright admit her feelings to Emma, Regina knocked on Snow's door, interrupting brunch. David answered the door with a smile and allowed both Regina and Henry in. After exchanging pleasantries with the Charmings, baby Neal, and Emma, Regina made her request.

"Snow, David," she said, "would you mind watching Henry today and allowing him to sleep over tonight? I have plans."

Henry rolled his eyes. This was not what he had pictured.

Emma immediately sprung up from her seat at the kitchen table.

"What plans do you have that will take all day and all night?"

Henry had to keep himself from laughing at his ma's blatant jealousy.

"That's none of your concern," Regina lied. It wouldn't do to spoil her surprise.

"I think I have a right to know," Emma insisted. "And why can't I watch the kid?"

"It's my week with Henry and I know how much you like to have your alone time, so I thought I was doing a favor."

"So you decided to ask my parents?"

Henry and Snow and Charming, sick of this back and forth and ready for the two women to just admit their feelings for each other all broke in simultaneously:

"I wanted to spend time with baby Neal."

"We would enjoy getting to spend more time with Henry."

"It's been quite a while since Henry's stayed over, I'm sure Neal and David would love another boy to play with."

Emma stared at her family as if they'd betrayed her and then she looked at Regina. "Fine," she said. "Enjoy your night."

As Regina watched Emma huff back to her spot at the kitchen table and resume angrily eating her scrambled eggs, she felt bad about being the cause of Emma's foul mood. But, she reasoned, if all went according to plan, Emma wouldn't be in a foul mood for long.

"I plan to," Regina said as she left the Charmings' apartment.

* * *

Regina had spent the day getting meticulously ready for her evening. She had shaved and waxed in all of the places that needed to be shaved and waxed. She had showered twice. She had painted her nails a brilliant shade of red. She had applied a matching shade of lipstick, but decided to forego any other makeup. It wasn't quite necessary for what she had planned, and she knew Emma liked her more natural look. The blonde had said so on more than one occasion.

Finally, Regina donned the red lingerie she had purchased so long ago during that trip to Boston. The bra fit her breasts perfectly and the skimpy panties hinted at all of the right things. Covered by the sheer red negligee, Regina knew she looked absolutely seductive.

Magically transporting herself to Emma Swan's room, she arranged herself in a very appealing pose.

Luckily, Henry had done a little reconnaissance for her and told her Emma's schedule precisely. So at 6:02 when Regina heard keys in the front door, she was not surprised. She heard Emma grumbling as she made her way to the bedroom.

The light was still off in the room and the sun had just set, so the room was quite dark, which explained why Emma did not see her when she first opened the door.

"She's probably out having the time of her life with _some guy_," Regina heard Emma mumble to herself before the light switch was flipped and the room was bathed in fluorescent lighting.

"Unless you've got something to tell me, _Emma," _she drew out the blonde's name, "I'm pretty sure I'm not going to be with _any _guy tonight."

Emma dropped her phone. Regina was certain it cracked. But Emma did not look like she cared as she took in the vision of Regina on her bed. Slowly, as if scared Regina was an illusion that would disappear if she approached her too quickly, she drew neared to the bed.

"What are you doing?" she whispered, her voice carrying no trace of suspicion, just a guarded wariness.

"I'm taking what I've wanted for a long time," Regina stated before considering her position. She was not taking what she wanted, actually. She was splayed out on Emma Swan's bed in a very vulnerable position, both physically and emotionally. She was offering herself up, to Emma, to love, to the Savior. If she had been more religiously inclined and currently not planning on being ravished by the blonde, she'd have laughed at the similarities this had to an official sacrifice to a god, had she, too, been a virgin.

But then again, she thought, aside from at her own hands, she'd never before been brought to climax by anyone, so in a sense she was almost like a virgin, waiting to experience the sexual pleasure she could gain at another's actions. And she was certain that unlike her previous bedfellows, Emma Swan would not disappoint.

So she restated her claim, "I'm offering myself up to you, Emma. I want you, so here I am. Your move."

And both women smiled at the reference to an earlier time in their relationship. But instead of butchering her tree, Emma Swan did something a lot more pleasurable to Regina's _forbidden fruit. _

* * *

After hours of vigorous sex and tender lovemaking, Regina and Emma were both spent.

"You know," Emma panted, "out of all your outfits, I think I like what you're wearing right now the best."

Regina looked at Emma, "Nothing?"

"Me."


End file.
